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133163-28-7 molecular structure
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2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

ChemBase ID: 96
Molecular Formular: C12H18N2O4
Molecular Mass: 254.28232
Monoisotopic Mass: 254.12665707
SMILES and InChIs

SMILES:
OC(c1c(OC)ccc(OC)c1)CNC(=O)CN
Canonical SMILES:
COc1ccc(cc1C(CNC(=O)CN)O)OC
InChI:
InChI=1S/C12H18N2O4/c1-17-8-3-4-11(18-2)9(5-8)10(15)7-14-12(16)6-13/h3-5,10,15H,6-7,13H2,1-2H3,(H,14,16)
InChIKey:
PTKSEFOSCHHMPD-UHFFFAOYSA-N

Cite this record

CBID:96 http://www.chembase.cn/molecule-96.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide
IUPAC Traditional name
midodrine
Brand Name
ProAmatine
Synonyms
Midodrina [INN-Spanish]
Midodrine HCL
midodrine hydrochloride
Midodrinum [INN-Latin]
Midodrin
Midodrine
CAS Number
133163-28-7
PubChem SID
160963559
46507373
PubChem CID
4195

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00211 external link
PubChem 4195 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.765054  H Acceptors
H Donor LogD (pH = 5.5) -3.4449556 
LogD (pH = 7.4) -1.7617897  Log P -0.95194644 
Molar Refractivity 66.2238 cm3 Polarizability 26.112099 Å3
Polar Surface Area 93.81 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.49  LOG S -1.76 
Solubility (Water) 4.45e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Soluble expand Show data source
Hydrophobicity(logP)
-0.5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00211 external link
Item Information
Drug Groups approved
Description An ethanolamine derivative that is an adrenergic alpha agonist. It is used as a vasoconstrictor agent in the treatment of hypotension. [PubChem]
Indication For the treatment of symptomatic orthostatic hypotension (OH).
Pharmacology Midodrine is a prodrug, i.e., the therapeutic effect of orally administered midodrine is due to the major metabolite desglymidodrine formed by deglycination of midodrine. Desglymidodrine diffuses poorly across the blood-brain barrier, and is therefore not associated with effects on the central nervous system. Administration of midodrine results in a rise in standing, sitting, and supine systolic and diastolic blood pressure in patients with orthostatic hypotension of various etiologies. Standing systolic blood pressure is elevated by approximately 15 to 30 mmHg at 1 hour after a 10-mg dose of midodrine, with some effect persisting for 2 to 3 hours. Midodrine has no clinically significant effect on standing or supine pulse rates in patients with autonomic failure.
Toxicity Symptoms of overdose could include hypertension, piloerection (goosebumps), a sensation of coldness and urinary retention. The single doses that would be associated with symptoms of overdosage or would be potentially life- threatening are unknown. The oral LD50 is approximately 30 to 50 mg/kg in rats, 675 mg/kg in mice, and 125 to 160 mg/kg in dogs. Desglymidodrine is dialyzable.
Affected Organisms
Humans and other mammals
Biotransformation Thorough metabolic studies have not been conducted, but it appears that deglycination of midodrine to desglymidodrine takes place in many tissues, and both compounds are metabolized in part by the liver.
Absorption Rapidly absorbed following oral administration. The absolute bioavailability of midodrine (measured as desglymidodrine) is 93% and is not affected by food.
Half Life The plasma levels of the prodrug peak after about half an hour, and decline with a half-life of approximately 25 minutes, while the metabolite reaches peak blood concentrations about 1 to 2 hours after a dose of midodrine and has a half-life of about 3 to 4 hours.
Clearance * Renal cl=385 mL/minute
References
Hebenstreit G: [Treatment of hypotension caused by psychopharmacological drugs (author's transl)] Wien Med Wochenschr. 1981 Feb 28;131(4):109-12. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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  • • Hebenstreit G: [Treatment of hypotension caused by psychopharmacological drugs (author's transl)] Wien Med Wochenschr. 1981 Feb 28;131(4):109-12. Pubmed
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PATENTS

PATENTS

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INTERNET

INTERNET

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